title: Amination of heteroaryl chlorides: palladium catalysis or SN Ar in green solvents?
abstract: The reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SN Ar reaction and N-arylation. The reaction is less satisfactory with pyridines unless an additional electron-withdrawing group is present. The results showed that the transition-metal-free SN Ar reaction not only compares favourably to palladium-catalysed coupling reactions but also operates under environmentally acceptable ("green") conditions in terms of the base and solvent.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD UK.
authors.forename: Katie
authors.initials: K
authors.lastname: Walsh
authors.forename: Helen F
authors.initials: HF
authors.lastname: Sneddon
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Moody
mesh_terms: D000586:Amination; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D055772:Green Chemistry Technology; D006571:Heterocyclic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D012997:Solvents; D002713:Chlorine; D010165:Palladium
keywords: amination; aromatic substitution; green chemistry; nucleophilic substitution